


Summertime (and the living is easy)

by flannelcastiel



Series: Swing!Verse [1]
Category: Supernatural
Genre: Alternate Universe - 1920s, Feminization, Flappers, M/M, Secret Relationship, Sexual Roleplay
Language: English
Status: Completed
Published: 2014-02-12
Updated: 2014-02-12
Packaged: 2018-01-12 01:37:25
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,323
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1180365
Author URL: https://archiveofourown.org/users/flannelcastiel/pseuds/flannelcastiel
Summary: <blockquote class="userstuff">
              <p>It is a scene Dean Winchester knows all too well.</p>
            </blockquote>





	Summertime (and the living is easy)

**Author's Note:**

  * For [BrandiChampane](https://archiveofourown.org/users/BrandiChampane/gifts).



> For [Brandi](http://bruisedcastiel.tumblr.com), who drew me [a pretty thing](http://jollycastiel.tumblr.com/post/66596549670/bruisedcastiel-for-katie-brandi-asdfghjkl-i) and I had to write a porny thing. For ultimate reading, listen to [this playlist](http://8tracks.com/medicinalmalaya/the-roaring-twenties#smart_id=tags:flapper+party+swing:safe&play=1)
> 
> Title is from Summertime by Billie Holiday

The haze of incense masks the odor of sweat and sex, making the low lit dive a little darker. Candlelight dangles from the ceiling—electricity is all the craze but it ruins the milky, warm atmosphere—making the skins of all in the club glow like the moonlight that would be shining inside if it had windows.

A band plays music that is all drums and trumpets and a bouncing piano that’s almost off key. Everything is off, from the dancers whose breasts were a little too small and whose thighs were thick with hair, to the businessmen who watched the tenacious boys in women’s clothing skimp around barefoot as they shook their hips to the music.

It is a scene Dean Winchester knows all too well.

When he arrives on a Thursday night, a night in which the city is drenched in the most awful spout of rain, he pays his way inside. Essentially, the fee is a silent bribe that seals the lips of any eye who might recognize him on the street. Sometimes he wonders if the other patrons recognize him: heir to the most prominent business in the city; he wonders if one would stay quiet only to avoid the innate wrath of his father. For once, Dean is grateful for John Winchester’s reputation. Though, if it was ever leaked to the press that he frequented places like these, he would be the first to be ruined. Or killed, depending on whether his father was feeling violent or gracious.

The hostess, a small woman with scandalously short black hair, takes his pinstripe jacket with a smile, her smeared red lipstick curling up into a smile as she regards him.

“Is he here?” he asks her beneath his breath, and he had been holding it.

She smiles even wider. “Waiting for you, Mr. Smith. Go on back.” He grins, face flushing at the mention of his pseudonym. It is a minute reminder if the taboo he is committing. Though the shame is short lived, eclipsed by an inexplicable excitement. He follows her back.

Back; back is that room that he pays for each week with his bonuses; the back room is where there are precisely four candlesticks illuminating the air, but a fireplace is centered against the back wall.

Dean sighs and closes the door firmly behind him, and then locks it. There is another door, which he leaves open. It’s the one Cas will come through.

He glances down at his watch, which tells him he has two minutes before his show begins. He wanders to a long table that is covered in hors d’oeuvres, most of which he won’t touch. But at the other in, he finds what he needs—the record player. He drops the needle and flips on a switch, making the disk spin. A smile pulls at his lips, as the drums start. It’s the same music that plays beyond these four walls of privacy, but nothing is off. It’s recorded perfection, a roaring trumpet rising like summer’s temperature and then falling like ice in a hailstorm.

Dean body sways to it, even though he has no rhythm. He never has, never will.

Another quick glance to his watch tells him it’s time to take a seat. As he moves to his chair, he undoes his belt and lays it aside. Once comfortable, Dean lets his eyes flutter shut, feeling an anticipatory high overwhelm him.

And then the hinges of the door squeak open.

A bolt of wanten electricity bolts up Dean’s spine as he watches Cas slowly slink through the door.

It is already too warm, fire calling sweat and making his face shine against the candlelight.

All of his attention is on Cas as he strides toward Dean, the heels of his ridiculously narrow shows clicking in Dean’s ears. His eyes flick to Cas’s feet and then slowly pan up his legs, his flat tummy extenuated by the ivory dress.

Cas pivots his hips as a horn drawls a note that’s deliciously off key. “Mr. Smith,” he says firmly, eyes never leaving Dean’s. Cas saunters a few more steps toward the armchair in which Dean rests in, catches Dean’s dangling hand and brings it to his mouth. The man’s lips, which are so pink that Dean might think they bare lipstick (but that cannot be so, because Dean requests that Cas wear no makeup), draw across his knuckles so gently. The innocence of it is tainted when Dean feels the occasional flick of a tongue, not like a cat’s but still rough, which injects a new flare of eroticism into the warm room.

“Cas, baby,” Dean whispers, pulling away from the man’s hand with a pained expression. Cas reflects it for a beat, shame stemming from some perceived disappointment in Dean’s eyes, but Dean quickly twists his hand and catches Cas by the cheek. Dean’s thumb rubs against the top of his cheekbone, not bruisingly but not gentle either, before letting go. “Dance for me.”

The request comes out like a dry, coarse demand, one that makes Dean’s skin go cold. Cas licks his lower lip, all forms of lewd, and takes a simple step back. His blue eyes are no more, fluttering shut as he pivots his hips—a blind man searching for leverage, a dancer looking for the hidden rhythm.

Suddenly, the song changes to a syncopated drum pulsing in the small space. Cas begins to thrust his hips, and Dean’s interest suddenly becomes focused solely on them. Underneath the dress, Cas’s hipbones press against his skin, noticeable through the sparkling white number. The hem of the dress, barely long enough to cover Cas’s ass (unfortunately), is wear Dean’s eyes linger—it is there, where sparkling beads dangle and swirl with the slightest movement, that Dean stares and stares until his eyes go dry and he must blink.

Cas apparently notices, and he chuckles. The low, obscenely coarse noise catches Dean’s attention, too, and he looks up to find Cas smiling at him.

“You like what you see?” he asks he rolls his shoulders, one stray arm stretching up above, fingers reaching for something invisible yet infinitely desirable.

Dean rumbles, “I always do.”

“Mhm,” is all Cas cares to reply as the song begins to slow. It makes time slow as well, and Dean is composed of impatience: his cock aches from the press of it against his zipper.  He shifts in his seat, summoning all his self-control in order to not palm himself. If he’s not careful, the simple rocking of his hips might cause enough stimulation to make him come. That is how erotic his little dancer is.

“Please,” Dean finds himself whispering, almost too low for Cas to hear—but he does. The dancer’s head tilts in that curious way, as if Dean is the anomaly, the freak. Maybe he is, for enjoying this—for having a man as he is expected to have a woman.

“You used to possess so much resolve, Mr. Smith.”

A breath, maybe two, and Cas is nearly on top of him. His legs spread, causing his dress to ride up high on his thighs, and he straddles Dean in his chair. Dean gasps at the sudden proximity, and he arches in the chair in an instinctive attempt to escape it. But Cas smells so good, like burnt firewood and mint. He relaxes into the man, but still lets out a surprised gasp when Cas slides down into him, his cock grinding across his lower belly and then his cock.

“God,” Dean breathes, hands falling onto Cas’s side and holding him down for a prolonged, pregnant moment. Oh, if there wasn’t anything between them they would be aligned now—hot members pressed together, unlike any god ever meant to men to be. Dean bites his lower lip, filling with an ineffable heat that comes with the awareness of the dirtiness of the situation.

But, when he runs his hand up Cas’s thigh, underneath his dress, it’s clean; when digressive fingers catch on the silken panties and pull down, there is no wrongness swirling in his stomach. Oh, and the little breathy noise that puffs against his face—blue eyes just inches from his own—when he brushes his palm against the length beneath those panties… Dean is already completely lost, willingly so, never wanting to be found if this is what it means to be a wayward son.

In an attempt to maintain the rouse, Cas wraps his fingers around the collar of Dean’s dress shirt and sways to the music, too quiet to even matter, breathing hard against Dean’s lips. It’s only a matter of time until they bump lips, so Dean simply lifts his chin and cover’s Cas’s mouth.

“Dean,” Cas whimpers a little into it, hips falling into Dean’s, which forcibly thrusts the length of his cock through Dean’s fist. The man shudders and wriggles, and Dean moans into his mouth. The obscene fluid coating his palm drips from finger to finger, and he wipes it against Cas’s thigh.

“Gotta get out of these pants,” he grunts against Cas’s mouth, and the man silently nods against him. He makes fast work of sliding off Dean’s lap just enough to unbutton his pants. Dean raises himself—both of them, in fact, but he’s desperate enough—so that the pants slide off with ease. It’s even easier to remove his boxers, already soaked in the front with the fluid of his arousal.

Eagerly, Cas grasps at his cock’s base and give a playful tease, which causes a string of curses to break from Dean’s lips. He gives a few strokes, smooth yet intensely blinding that makes it all feel rough, before placing his lips over Dean’s again.

“You,” Dean mumbles, daring not to let Cas pull away. “You’re amazing.”

Cas hums, not as chalant as he tries, in response and uses one hand to cup Dean’s face, the other to pull both of their lengths together. Enthralled by the sensation of hot, soaking skin thrusting past each other, Dean breaks the kiss to watch their cocks move against each other while Cas thrusts his hips. He begins to feel a familiar, ferocious fire burning and coiling like an armed explosive in his stomach. White begins to crawl from the outskirts of his vision and Cas’s groans almost seem to harmonize with a trumpet blaring in the background.

Dean comes first with a grunt, enamoured by the sight of white liquid spewing from his cock onto Cas’s dress. Fleetingly, he wonders if that’s why Cas wears white—

The thought is entirely short lived when Cas grinds down into him, his cock exploding with come all over Dean’s, mixing with his own spent arousal.

Their foreheads fall together, panting breaths mixing when their lips join eventually, too.

 

* * *

 

Friday mornings, traditionally, are composed of long, boring board meetings, of which Dean is a chairperson. His father sits at his left, and the chair to the right remains empty. A window on the far side of the room allows a brief moment of sunlight to shine through before the sun is eclipsed by a gray cloud, a sign that winter is truly among them.

Dean decides that the least of his good qualities, yet the most frequent, is his impatience. His fist clenches beneath the table against his thigh.

When the hinges of the conference room door groans as it opens, Dean turns his head on instinct. Simultaneously, he feels as if he is being warmed by a churning fire and being splashed with a tub of ice.

“Good morning,” says his colleague, his friend, as he takes his regular seat next to Dean.

He wears a better mask than Dean could ever hope to have; Castiel has always had a way of reversing the cliche—an open book. Instead Castiel is often shut tightly, only letting Dean’s fingers push through the delicate pages that detail both of their darkest fantasies.

“Mr. Novak,” Dean greets with a forced smile; Castiel returns it and Dean feels his cock give a deceivingly hopeful twitch.

John, on the other side of Dean, leans forward and nods his head a the man. “Good morning Mr. Novak. I expect that you were able to complete the report I assigned you?”

By way of response, Castiel reaches into the briefcase at his feet and finds a thick stack of papers. He could have just laid it on the table and pushed it at Dean to pass onto his father, but instead he reaches across Dean—the smell of his cologne gets hung up in Dean’s nostrils as a chill runs down his spine.

“Here you go, sir.”

John’s attention is taken by the reports, so he does not hear the rasp of breath between Dean’s teeth as Castiel’s falls and grazes Dean’s thigh.

“Mr. Winchester,” Castiel says with some calcified concern. “You seem terribly…high strung.”

The man is a bastard, an intolerable, callous bastard. Dean licks his lips, brows lowering warningly as he leans subtly toward Castiel.

“Long night,” he supplies with a distinctly bitter tone, careful not to let his own facade crack and reveal the itching of his fingers to stretch out and touch.

“Mhm,” Castiel replies with every bit of nonchalance, but Dean catches the twitch of his lips. It’s subtle, but Dean is fluent in the language of those lips. “You should retire earlier, as I do; you will be surprised what relaxation will do for you.”

Castiel strokes small circles around his knee, affectionate and soft and so secretive.

“I…I’ll keep that in mind.” Dean smiles at the man next to him, and if he lets the sounds of papers flipping fade, the thrumming of his pulse fades into the sound of a drum—and, from there, it isn’t a stretch to imagine the trumpets, the piano, and of Cas dancing beatlessly next to him.


End file.
